


Betcha Can't Make an Alpha Cry

by Ookamisan



Series: Sexathoning [1]
Category: Teen Wolf (TV)
Genre: Alpha Derek, Blow Jobs, Bottom Derek, Come Marking, Come Shot, Hand Jobs, Knotting, M/M, Oral Sex, Overstimulation, Praise Kink, Prostate Massage, Prostate Milking, Rough Sex, Sex Toys, Spanking, Tickling, Top Stiles Stilinski, Vibrators
Language: English
Status: Completed
Published: 2016-08-04
Updated: 2016-08-04
Packaged: 2018-07-29 08:45:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,560
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7677772
Author URL: https://archiveofourown.org/users/Ookamisan/pseuds/Ookamisan
Summary: <blockquote class="userstuff">
              <p>Derek is utterly bored by the idea of bottoming and doesn't take Stiles's word about anal seriously. Turns out Derek is kind of a slut for Stiles's dick and Stiles gets a major power trip over it.</p>
            </blockquote>





	Betcha Can't Make an Alpha Cry

**Author's Note:**

> I havent actually found a fic yet where Derek bottoms and just loses all his brain cells and becomes a total moany slut for Stiles. So I had to write one obviously.  
> Im not sure how I feel anout it but ey.  
> Non beta'd.

"You're way too excited." Derek watched with an eyebrow raised as his boyfriend practically pranced around their bedroom in his underwear, grabbing supplies for their night.

"Derek I have every reason to be _flying high_  right now." Stiles said as he dumped condoms, lubes and various toys of various sizes on the bed. "You have never bottomed before. This is going to be amazing!"

Derek sighed and rolled his eyes from where he was perched at the end of the bed, arms crossed and looking horribly unimpressed, still wearing his t-shirt and boxerbriefs. "Jesus, Stiles it cant be _that_ amazing."

Stiles looked affronted. "Have you SEEN my face when you fuck me? I am very well experienced in the bottoming area and-"

"Well thats _me_ __fucking you. I just dont see the appeal, really." He picked up one of the toys and studied it. "What the hell is this anyway? Honestly it looks like a torture device."

"Yes." Stiles said flatly, taking the stainless steel prostate stimulator away and tossing it towards the pillows.

"Yes, what? Yes it's a torture device? Stiles I'm worried already." Derek stared at his boyfriend.

"It is the best kind of torture device, my child-" "Dont call me child." "-Maybe we will get to it tonight, but for now, let's play. You did wash and clean yourself right?"

"Yes, Stiles, of course I did."

"Good! Let's go!" Stiles enthusiastically threw his arms round his boyfriend's neck and kissed him. The kiss started off clumsy and playful despite Derek's unenthusiastic attitude about the whole thing. However after a few minutes, the kiss went to soft, tender kisses and eventually became passionate and firey as Derek naturally took over and pinned Stiles to the bed.

Derek made himself at home between Stiles legs, but Stiles pulled away from the kiss when Derek ground his slowly filling cock into Stiles's bum.

"Nah-uh! Remember what we're doin here?" Stiles smacked Derek's shoulder lightly as he made to get up. "And lose the clothes!"

Derek sighed at being denied his regular booty grinding and pulled the t-shirt over his head and tossed it to the floor where his boxerbriefs joined it. He reclined back on the pillows with his arms behind his head, trying to get comfortable and... in the mood. He looked doubtfully at his barely chubbed dick laying lazily against his hip as Stiles picked up a pink bullet vibrator that they rarely used, and the lube.

"Now that won't do." Stiles said, gesturing to Derek's very sleepy looking cock as he kneeled between Derek's legs.

Stiles squirted some lube into his hand and while he warmed it between his fingers, he bent down to lick tentatively at the head of Derek's dick.

Derek sighed and closed his eyes at the familar feeling of Stiles's kitten licks, his dick slowly waking and showing interest.

Stiles swiped his lubed fingers across Derek's hole in a swift, efficient manner. Derek jumped a bit and then relaxed as Stiles left it alone and continued his task of blow job.

Stiles actually spent a good amount of time just treating, aka teasing, Derek with swipes of his tongue around the head. Making it shine and drip.

Derek was really aware of the cold air around his hole because of the lube and he almost wondered if Stiles had forgotten about it, when he finally enclosed his mouth around the head and pressed his knuckles against Derek's entrance.

Derek flinched, then held back the small moan at having pressure on his hole while his dick was in Stiles's hot mouth. He exhaled slowly as Stiles took more of him into his mouth, and simultaneously began rubbing his knuckles along Derek's entrance.  
After a minute or so of having the stimulation from his knuckles, Derek was struggling to not wiggle.

All of a sudden there was more lube and Stiles had inserted a finger. It didnt feel like much.

Derek wasn't impressed.

When Stiles stuffed in a second finger however, and twirled his tongue around Derek's head, he had a little harder time holding back his moan.

Stiles smirked up at him and pulled off and out, letting Derek catch his breath. "I told you it was awesome."

Derek actually had the nerve to laugh. "I make more noise fucking you."

Stiles scrunched up his nose and, grumbling to himself, picked up the bullet vibrator. He slowly eased it into Derek, who didnt react at all to it.  
Until Stiles turned it on.

At first he didnt feel much, but as Stiles turned the dial up, suddenly Derek was having a bit of difficulty keeping still.

Stiles smirked again, feeling victorious at Derek squirming and clenching his teeth in obvious ecsta-

"AHAHA! S-STILES TURN I-IT OFF IT TICKLES LIKE A MOTH-AHHAHA!" Derek was now writhing and practically crawling up the bed frame trying to get away.

Stiles turned it off and pulled it out a little non-too-gently. "What the hell, Derek! How in the hell- That always feels amazing to me how in the world?"

Derek's face was bright red from losing his composure. "It's not my fault you are into weird vibrating shit."

Stiles huffed. "Fine lets just stick to fingers, then."

After that little hiccup it took them both a minute to regain the mood and chemistry, but eventually Stiles had Derek open loosely on three of his fingers while he sucked on Derek's balls passionately.

Derek never knew why watching Stiles suck and lick his balls gave him such a power trip but it always did, and right now he was slowly rocking his hips up into Stiles's mouth while giving quiet little grunts of pleasure and sighing, "yeah"s and "mhm"s. He had to admit that the stretch of three fingers was adding something to his normal arousal, but he still wasn't convinced about it being the best thing ever. He thinks mostly Stiles is just a drama queen that really wants to top. Which Derek doesnt mind, obviously. There's just nothing special about-

"Uhn!" Derek jumped as Stiles had purposefully pressed upwards, and there had been a sharp wave of, not quite pleasure but not pain. His dick however seemed to appreciate it as it pulsed particularly strongly.

Stiles carefully pulled his three fingers out partway and squeezed in a fourth.

Derek groaned a little at just how much stretch he was experiencing down there. "Stiles, I dont mean to be rude but your dick is not the size of a watermelon. Is this much stretch really necessa-aeeee!" Stiles curled all four fingers up into the bundle of nerves and did. not. stop.

"Im being nice to you, dummy." Stiles spanked Derek's cheek on the word "dummy", and Derek felt heat pool in his belly. Wow, really? Spanking is a thing for him?

Derek bit down on his lips as Stiles seriously would not stop stimulating his prostate. Constant little swipes back and forth making the weird feeling turn into a dull burning at the base of his dick. His breath started coming out in short, harsh huffs and he was arching his head back, his legs threatening to spread and lift.

"Found it." Stiles said in a "i told you so" tone.

Derek actually managed to pout and glare at him, but refused to open his mouth for fear of moaning like a slut.

Stiles took it as a challenge and changed from swiping, to pushing up and fucking Derek on his hand, teasing at the idea of fitting his thumb in.

Derek scrunched up his face, clenching his teeth and honestly probably looked more constipated than overwhelmed with new sensations. His cock was rock hard and angry looking against his abs as precum seemed to stream out endlessly, spilling over his hips.

Stiles suddenly pulled out, looking frustrated, and grabbed one of the condoms. "It wont kill you to make noise, yknow. It feels fucking awesome, admit it."

Derek said nothing as he tried to catch his breath and refrain from wiggling like the empty whore he felt like.

Stiles slid the condom and some lube on, and surprised Derek by scooping up his legs and actually pulling him down to Stiles hips where he wanted him. Okay so add being manhandled to his kinks.

Stiles found Derek's entrance and slowly pressed his way inside. Derek opening his mouth in a little "o" as the flared head popped passed his rim.

Derek had never really thought about the length or width of Stiles's dick. But right now as it filled him, he swore Stiles was massive. He took deep steadying breaths as Stiles's hips pressed flush to his ass.

Stiles groaned as he was engulfed and after a few moments, ground his hips in a circular motion, not quite pulling out.

Derek's reaction was to tense up, biceps bulging as he gripped the comforter when Stiles's dick pushed up on his prostate. His own dick flexed and seemed to bulge as blood rushed to it, turning it dark and swollen.

As Stiles eased out and pushed back in, brushing over his prostate again painfully slowly, Derek couldn't hold back the uncharacteristically high moan that left his throat, a large blob of precum lazily spilled down his shaft.

Stiles's pupils bloomed and, bracing himself around Derek's hips, began a hard pace. Immediately Derek began to whine more as the friction slowly burned his hole in the best way possible, blushing as he felt his rim become frothy and loose.

As Stiles picked up his pace, Derek steadily became more and more vocal. When Stiles leaned back, taking Derek's hips in a tight grip, fucking up directly into Derek's prostate, Derek screamed hoarsely and gave into the feeling, spreading his legs wide and pressing back into Stiles as best he could.

"Fuck. Yes, Derek!" Stiles growled, watching his boyfriend fall apart underneath him. "You like me fucking your prostate?"

Stiles didnt actually expect Derek to open his eyes and hold eye contact, nodding desperately as he was jostled up the bed.

Stiles paused to bend Derek's legs to his chest, holding him behind the knees, just like Derek always did to him, and pounded even harder into Derek.

"You like it, Der?"

"Yeahh." Derek whined.

"You like my cock fucking pounding you? You believe me now?"

"Uh-huh."

Derek's cock was dark red with an angry, bulbous head that was turning purple and constantly leaking cum. When Stiles slammed in and stayed still, Derek's cock was pulsing desperately, looking like it was going to explode at any second.

Stiles leaned down to kiss Derek, who actually pulled away and shook his head. "No, no, I want to cum. Please Stiles, I wanna cum." He tried to rock his hips against Stiles desperately. His voice airy and breathless.

"Do you now?" Stiles cupped Derek's tense balls under his thumb, pushing on his scrotum. Derek whined high and reached to cup his dick. Stiles immediately knocked his hand away. "Good boys cum when they are told."

Derek groaned frustratedly and screwed down viciously on Stiles's dick, making him yelp. "Ngh! Hey!"

Derek took the opportunity to push Stiles onto his back, and straddle him, lowering himself back down onto Stiles's cock, moaning at how gravity forced Stiles deeper.

"That's not fair, Derek."

Derek braced himself by Stiles's sides, arched his hips and began to brutally fuck himself on Stiles's cock, moaning like a whore and drooling.

Stiles clenched his teeth and held on for dear life as he was flown to the edge, arching up into Derek as he came.

Both he and Derek groaned at the feeling and Derek desperately began to strip his cock in his fist like he was trying to hurt himself. Just as he was about to cum, Stiles pushed him off and onto his back, pinning his hands.

"Fucking hell, Stiles!" Derek snapped, his cock spurting precum and drooling.

"Just, hold on," Stiles picked up the thick prostate stimulator, quickly lubed it, and inserted in into Derek's hole, then sat back to watch.

As soon as the stimulator rested against his scrotum, Derek's eyes shot wide. At first he rolled his hips like he wanted to desperately fuck into something. Not being able to escape the feeling of his prostate being stimulated. His hole clenching around it, and therefore milking his own prostate without even trying. Derek moaned loud and dug his fingers into the sheets.

Stiles discarded his condom and stroked his half hard cock lazily, arousal blooming once again at his boyfriend writhing in ecstasy.

Derek's cock looked painful and suddenly Derek leaned up on his elbows to stare down at himself and then at Stiles. "Ohh my god! Stiles!"

Stiles wasnt sure what the problem was for a moment until suddenly the base of Derek's dick began to swell and throb visibly. "What the-"

"It's my knot! Ohhh fuck, Stiles! I havent knotted since... Ohhh shit!" Derek collapsed back and thrust his hips upwards repeatedly, desperately fucking the air as his hands clenched and shook with the need to touch himself, but knowing it would be too painful.

Stiles crawled over to Derek and slid his palms up Derek's thighs soothingly and shushing him. It didn't do much to stop the trembling but Derek spread his thighs to allow Stiles in.

Stiles bent over Derek's hips and enclosed his mouth around the tip, pressing his tongue against the underside of the head, earning him a spurt of precum and Derek panting and crying out.

"Ah! S-Stiles!" Stiles pressed the tip of his tongue into Derek's slit and gently enclosed the bulbous knot in both of his hands.

"FUCK! Harder!" Derek clamped one of his hands in a vice over Stiles's hands and squeezed so hard that Stiles's fingers cramped. Derek roared, arched his hips and came in Stiles's mouth, which quickly overflowed and streaked across his face and neck.

Stiles couldnt escape because of Derek's death grip on his hands, so he was left to duck his face into the mattress trying to stifle his laughter as that wouldn't be very nice to do while Derek is in mid-orgasm.

When Derek finally came down from his high and released Stiles's hands, his cock flopped wetly onto his abs, still oozing cum.

Stiles got up from the bed and brought in a wet washclosh to mop Derek down. "Oh my god these sheets are never going to be the same." Stiles smiled down at the barely conscious werewolf.

When they both had changed the sheets and showered, they lay in bed enjoying the ache that came after fucking so brutally and exercising.  
"I told you anal sex is the bomb."

"It was ok." Derek smirked.

Stiles looked at him, feigning insulted. "I made you cry from pleasure you asshole!" He aimed a pillow at Derek's face, who laughed and batted away the attack.

"Yes you did. And next it'll be you crying on my dick."

"We'll see." Stiles taunted, settling back into the sheets.

"Is that a challenge?"

"You're on. Whoever can make the other cum or cry first wins."

"I will definitely make you cum before you make me cry." Derek pulled Stiles in close, nuzzling his neck that smelled of fresh shampoo and still a bit like Derek, and sighed, feeling more content than he had in a very long time.


End file.
